New Windsor Holidays

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Your New Windsor Holiday

There's no better way to travel than with one of our holiday packages to New Windsor. The rich history and spectacular views are two of the convincing reasons to spend some time in this captivating city. Dia Beacon, Storm King Art Centre and Ice Time Sports Complex are just some of the attractions you'll want to explore during your trip to New Windsor. A couple of quick clicks is all it takes to put together a tailored New Windsor holiday on Expedia.

New Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
8,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, SplashDown Beach and Dia Beacon

Top hotels in New Windsor

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
The price is £78 per night from 22 Nov to 23 Nov
£78
22 Nov - 23 Nov
includes taxes & fees
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is £95 per night from 9 Nov to 10 Nov
£95
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very good! (1,010 reviews)
"A bit dated and worn. Signage could be better. But the setting is fabulous So beautiful in autumn!"

Reviewed on 4 Nov 2026

Overlook Lodge at Bear Mountain
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is £81 per night from 29 Nov to 30 Nov
£81
29 Nov - 30 Nov
includes taxes & fees
9/10 Wonderful! (1,159 reviews)
"Very clean, nice breakfast."

Reviewed on 4 Nov 2026

Hyatt Place Poughkeepsie / Hudson Valley
See all 1,050 properties in New Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular New Windsor attractions

National Purple Heart Hall of Honor

8.0/10 (11 reviews)
This solemn museum honours Purple Heart recipients with interactive exhibits telling their stories of sacrifice. Explore the "Roll of Honour" database to discover personal narratives through artefacts.
See properties

What to do in New Windsor

Woodbury Common Premium Outlets Shopping Tour from Midtown

Woodbury Common Premium Outlets Shopping Tour from Midtown

£41
per adult
96% of travellers recommend
Woodbury Common Premium Outlets Shopping Tour from Midtown
Limo Tour NYC to Woodbury Common Premium Outlets

Limo Tour NYC to Woodbury Common Premium Outlets

£970
per traveller
Limo Tour NYC to Woodbury Common Premium Outlets
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

£583
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in New Windsor

Frequently asked questions

How much does a New Windsor travel package cost?
Go from wondering to wandering with our New Windsor travel packages, which start from just . Pick the hotels and flights that suit your plans. Then, add on one or two experiences or tours to round off your unique escape.
If I'm not able to travel, can I cancel my New Windsor travel package?
Don't worry if you're rethinking your New Windsor travel package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to New Windsor?
Combine your hotels and flights, throw in extras such as tours, and save with a New Windsor travel package. You won't just walk away with awesome discounts on your adventure — you'll have loads of choice at your fingertips too. When you book through Expedia, you can select from more than 550 air carriers and 1,000,000 hotels around the world. Your next big adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later New Windsor holidays?
Expedia has partnered with online lender Klarna to make your next getaway a bit easier on the wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you spot an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in New Windsor?
A holiday in New Windsor isn't complete without stopping by New York Military Academy, Mount Saint Marys College Newburgh and Washington Headquarters. Stay close to these sights and make sightseeing easy.
What are the top hotels in New Windsor?
Red Roof Inn & Suites Newburgh – Stewart Airport in the Vails Gate neighbourhood is a wonderful choice for a New Windsor holiday. Reserve a room here and you'll be well-placed to get out and explore all that this buzzing city has to offer.
How far in advance should I book my New Windsor holiday?
While not all air carriers advertise ticket prices early, you can usually look up international flights on Expedia up to 12 months in advance. This is when you can nab some incredible bargains. If you're booking last minute, there's a chance you could get lucky. Low prices occasionally emerge just weeks prior to departure.
What does an Expedia New Windsor travel package include?
With Expedia, you can choose a combination of flights, hotels and car rentals to build your perfect New Windsor travel package. Once you've made your booking, you can add on fun stuff like tours and experiences. Don't forget, the more you bundle, the more cash you'll save!
What should I know before booking a New Windsor travel package?
An Expedia travel package can be customized for your circumstances and is a simple way to make your money go further. How little or much you include is totally up to you. Rental cars, hotels and flights — mix and match whatever combination suits your style.
Can I choose my airline with a New Windsor Expedia travel package?
Expedia has access to more than 550 airline partners globally, so you certainly can. Just pick the carrier that suits you and craft the perfect New Windsor escape.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.